2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE

2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE Basic information
Product Name:2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE
Synonyms:2-Amino-5-bromo-6-phenylpyrimidin-4(3H)-one;2-AMINO-4-HYDROXY-5-BROMO-6-PHENYLPYRIMIDINE;2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE;2-Amino-5-bromo-6-phenylpyrimidin-4-ol;2-Amino-5-bromo-6-phenylpyrimidin-4(1H)-one;5-Bromo-6-phenyl-2,3-dihydro-2-iminopyrimidin-4(1H)-one;PNU-54461;U-54461
CAS:56741-95-8
MF:C10H8BrN3O
MW:266.09
EINECS:
Product Categories:Heterocycle-Pyrimidine series;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:56741-95-8.mol
2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE Structure
2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE Chemical Properties
Melting point 285-287° (Stevens); mp 246-248° (Brown, Stevens)
Boiling point 389.7±52.0 °C(Predicted)
density 1.6292 (rough estimate)
refractive index 1.6520 (estimate)
storage temp. room temp
solubility DMSO: ≥5mg/mL (warm DMSO)
form powder
pka3.18; 8.53(at 25℃)
color white to beige
Water Solubility 7.8mg/L(37 ºC)
Safety Information
Hazard Codes Xn
Risk Statements 63-62
WGK Germany 3
RTECS UW7351300
MSDS Information
2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE Usage And Synthesis
DescriptionBropirimine is an immunomodulator with diverse biological activities. It is a toll-like receptor 7 (TLR7) agonist that inhibits RANKL-induced osteoclast differentiation of murine bone marrow-derived macrophages (BMDMs) in a concentration-dependent manner, an effect that is reversed by an anti-IFN-β antibody. Dietary administration of bropirimine (200 mg/kg twice per week) prevents development of transitional cell carcinomas (TCCs) in a mouse model of carcinogen-induced bladder carcinoma. Bropirimine (100 mg/kg) reduces pulmonary collagen accumulation and bronchoalveolar lavage fluid (BALF) monocyte and eosinophil infiltration in a hamster model of bleomycin-induced lung fibrosis. It also delays disease onset and progression and increases plasma IFN levels in a mouse model of experimental autoimmune encephalomyelitis (EAE).
UsesBropirimine, an immunostimulating agent and toll like receptor (TLR7) agonist, is used in comparison with other TLR7 agonists such as imiquimod, R-848, loxoribine in interferon cell signaling research. Bropirimine may be used in experimental autoimmune encephalomyelitis (EAE) and bladder cancer research.
UsesBropirimine is an orally active immunostimulant; anticancer agent. Bropirimine is an interferon inducer that is a potentially useful in the the treatment of superficial bladder cancer (transitional cell carcinoma). Studies suggest that Bropirimine has direct antitumor activity rather than a cytokine-mediated antitumor effect.
DefinitionChEBI: Bropirimine is a member of pyrimidines.
Biochem/physiol ActionsBropirimine is an immunostimulating agent. The compound induces production of α and β interferons and enhances NK cell function. Bropirimine has antiproliferative effects in cancer cell lines and tumor growth in in vivo models.
storageDesiccate at RT
2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE Preparation Products And Raw materials
Bromisoval Neostigmine bromide Mestinon 2-Amino-4-methyl-5-bromopyrimidine 5-Bromo-4-phenylpyrimidine 2-AMINO-5-BROMO-4-HYDROXY-6-METHYLPYRIMIDINE 5-bromo-1H-pyrimidin-4-one 2-Amino-4-hydroxy-6-phenylpyrimidine 2-AMINO-5-BROMO-4-HYDROXY-6-PHENYLPYRIMIDINE N2-ACETYLAMINO-4-HYDROXY-5-BROMO-6-PHENYLPYRIMIDINE 2-Amino-5-bromopyrimidine Pyrimidine, 5-bromo-4-methyl- (7CI,8CI,9CI) 5-BROMO-6-METHYLPYRIMIDIN-4-OL 2-AMINO-5-BROMO-4-PHENYLPYRIMIDINE 2-amino-5-bromo-4-pyrimidinol

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